The earliest example I know of comes from the days of warships with sails and black-powder cannon. Two cannon balls joined by a length of chain were fired into another vessel's sails These would cut ropes, entangle all sorts of rigging, and possibly bring down masts.
“The earliest example I know of comes from the days of warships with sails and black-powder cannon. Two cannon balls joined by a length of chain were fired into another vessel’s sails These would cut ropes, entangle all sorts of rigging, and possibly bring down masts. “
As I understand, this was often done with two cannons, not two balls in one cannon. I imagine a misfire or late fire on one could have disastrous effects.